Olenicoff was born in Moscow in 1942. After the war, his family being tsarists, fled the Soviet Union for Iran where he was educated by missionaries. In 1957, his family emigrated to the United States. In the U.S., his Father Michael, an Engineer, worked as a janitor, and his mother, Zina, worked as a housekeeper. He graduated from the University of Southern California with an undergraduate degree in corporate Finance and mathematics as well as an M.B.A.

After school, he worked as a consultant and corporate executive. In 1973, he purchased a 16 unit duplex with his newly founded company Olen Properties. Since then, he has grown the firm and now owns more than 6.4 million square feet of office space and nearly 12,000 residential units in Las Vegas, Arizona, California, and Florida.

Sentencing guidelines called for a prison sentence of up three years, which typically resulted in a sentence of six months, but the federal prosecutors advised against sending Olenicoff to jail. The U.S. probation officer submitted recommended that Olenicoff receive a sentence of one year on probation, while the prosecutor's memorandum recommended probation for three years. While the prosecutor admitted that Olenicoff had cooperated with the government as per the terms of his plea bargain, he had illegally used off-shore banks to avoid taxes since at least 1992.” Assistant U.S. Attorney Brett Sagel argued that a shorter probation period would enable the Billionaire to speedily repatriate his assets, which currently were out reach of the IRS.

According to Forbes, the IRS was investigating Olenicoff for tax evasion. The IRS contended that Olenicoff was the sole owner of Olen and used Bahamas-domicled Sovereign Bancorp Ltd. as an offshore vehicle to hide assets from the IRS and his creditors in order to evade taxes. Olenicoff denied he owned Sovereign, claiming that it was a Russian parastal investment vehicle established by Boris Yeltsin, and that it had merely lent money to Olen. The IRS hit Olenicoff with a $77 million for back taxes and penalties for the years 1996 and 1997 and was investigating him and Sovereign for the 2002 and 2003 tax years.

Olenicoff was ensnared in the UBS scandal, in which the Swiss private bank was revealed to have helped American citizens evade billions of dollars in taxes owed to the U.S. government. Olenicoff was recruited to UBS from Barclays Bank by Brad Birkenfeld, who subsequently blew the whistle on UBS's abetting of tax evasion by wealthy Americans. Olenicoff became a client of UBS in 2001, and transferred $200 million to the bank using credit cards supplied by Birkenfeld.

Olenicoff is married to Jeanne M. Patterson, a Los Angeles native. They have two children: Andrei and Natalia. Andrei was killed in a car accident in 2005. Andrei suffered from retinitis pigmentosa and the Olenicoffs founded the Andrei Olenicoff Memorial Foundation in his honor. As of December 2010, Igor Olenicoff was listed as the Newport Beach, CA-based private foundation's President. It gave out $37,890 in grants and had assets of $208,859.

In 2006, Forbes Magazine estimated his fortune at $1.6 billion, based upon his sole ownership of Olen Properties. However, Olenicoff told the magazine that he did not own the company, claiming that it was owned by an offshore company–incorporated company since 1980. Olen's offshore corporate parent was first headquartered in the Cayman Islands, the Bahamas and Denmark.

In December 2007, Olenicoff pleaded guilty to a single felony count of filing a false tax return for 2002. He admitted to tax evasion and of misleading the IRS about his offshore accounts in the Bahamas, Liechtenstein, Switzerland, and the United Kingdom. As part of his plea bargain, Olenicoff paid a $52 million fine and agreed to repatriate his offshore funds to the United States.

Since Olenicoff was sentenced in 2008, 63% of those defendants in offshore tax evasion cases have not been sentenced to jail.

Olenicoff also is being sued by Sculptor John Raimondi, who was contacted by the real estate tycoon to create versions of two of his extant sculptures as part of a percent-for-art mandate. If Olenicoff had followed through with commissioning the works, Raimondi would have made $100,000 to $250,000. Raimondi had supplied Olenicoff with detailed drawings and photographs of the proposed works, which Olenicof subsequently cancelled. In 2010, Raimondi was informed that sculptures that originally had been submitted to the city of Brea, California as being his works were now credited to a Chinese Artist. Raimondi had never authorized the creation or display of the sculptures he had discussed with Olenicoff.

In 2011, Olenicoff claimed that the sculpture and three others like it that were on display at other Olen sites had been bought in Beijing during the 2008 Olympic Games. Olenicoff also said he had one of the sculptures modified with the addition of a stainless steel form representing a teardrop. At the time, he refused to confirm or deny whether the sculptures were copies of Wakefield's original work. Wakefield's sculpture would cost $160,000 whereas the Beijing-made knockoffs would cost approximately $35,000 each.

In August 2012, UBS sued Olenicoff under California law for malicious prosecution. The lawsuit quoted Guilford's decision. The complaint claims, “In order to pursue his claim of fraud, he disavowed the sworn statements he made in the Criminal case acknowledging his own active deceit, and instead claimed he actually had been unaware that he had lied on his tax returns. This change of his story was done for the purpose of pursuing a false claim of fraud against UBS.”

Warner's pre-sentencing report that called for a jail sentence said his offshore account was the biggest ever found. In fact, the lawyer's pointed out, Olenicoff had illegally stashed $240 million offshore. The Olenicoff defense worked. On January 14, 2014, District Court Judge Charles P. Kocoras sentenced Warner to two years probation and 500 hours of community Service. The judge rejecting the prosecution's recommendation for jail time of one year and one day, to serve as a deterrent to other tax cheats. Olenicoff, who also got two years probation and community Service, pleaded guilty to filing a false tax return, a felony. Warner pleaded guilty to the more serious charge of tax evasion.

The major benefactors of the Andrei Olenicoff Memorial Foundation are the Foundation Fighting Blindness, Guide Dogs for the Blind, and Makapo Aquatics, a visually-impaired paddling team. One of their Foundation’s first gifts went to Russian orphans who needed prosthetic devices and corrective surgeries. His sister opened a restaurant in Irvine, California, called Andrei’s Conscious Cuisine and Cocktails. Natalia is married to Derek Ostensen.